Diisopropylethylamine → (R)-4-(5-methyl-7-oxo-7H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamide

HRID 908637Notes

Reaction equation

[F:1][C:2]([F:35])([F:34])[O:3][C:4]1[CH:33]=[CH:32][C:7]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][NH:16][CH2:15][CH2:14][N:13]2[S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[O:11])=[CH:6][CH:5]=1.Br[C:37]1[S:47][C:40]2=[N:41][C:42](=[O:46])[CH:43]=[C:44]([CH3:45])[N:39]2[N:38]=1.C(N(CC)C(C)C)(C)C>C(O)C>[F:35][C:2]([F:1])([F:34])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][N:16]([C:37]3[S:47][C:40]4=[N:41][C:42](=[O:46])[CH:43]=[C:44]([CH3:45])[N:39]4[N:38]=3)[CH2:15][CH2:14][N:13]2[S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[CH:23][CH:22]=2)(=[O:19])=[O:20])=[O:11])=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixed solution of the compound (0.038 g) obtained in Example 783, the compound (0.023 g) obtained in Step 3 and ethanol (1.0 ml) was added N,N-diisopropylethylamine (0.019 ml) at room temperature. After stirring at 100° C. for 3 hr, the reaction mixture was concentrated under reduced pressure, and the residue was purified by thin layer silica gel chromatography (methanol:chloroform=1:9) to give the title compound (0.032 g).

Workup

concentrationthe reaction mixture was concentrated under reduced pressure
customthe residue was purified by thin layer silica gel chromatography (methanol:chloroform=1:9)

Sources & evidence

ORD record: ord-64a817edf88946629a5376f73cde22fb
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017612B2

Reaction notes

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